4171-69-1

Usage

Uses

Used in Pharmaceutical Industry:
Benzyl 2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside is used as a reactant in the preparation of oligosaccharides and glucosamine-containing peptides. These compounds are specifically designed to act as inhibitors of influenza virus neuraminidase, a key enzyme involved in the replication and spread of the influenza virus. By targeting this enzyme, these inhibitors can help prevent the virus from infecting new cells, thereby reducing the severity and duration of influenza infections.
Additionally, Benzyl 2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside may also be used in the synthesis of other bioactive compounds with potential applications in various therapeutic areas. Its unique structure and reactivity make it a valuable building block for the development of new drugs and pharmaceutical agents.

Upstream product

• 7512-17-6 N-Acetyl-D-glucosamine 
• 100-39-0 benzyl bromide 
• 62098-37-7 benzyl 2-Amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 13435-12-6 N-Trimethylsilylacetamide 
• 100-51-6 benzyl alcohol 
• 4171-73-7 2-acetamido-1-O-acetyl-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranose 
• 65760-01-2 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl acetate 
• 19488-48-3 methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 3068-36-8 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitroanilino)-α-D-glucopyranosyl bromide 
• 7784-55-6 Tetraacetyl-<2,4-dinitrophenyl>-glucosamin 
• 111240-23-4 benzyl 2-deoxy-2-(2,4-dinitroanilino)-β-D-glucopyranoside 
• 871116-05-1 1,3,4,6-tetra-O-benzyl-2-deoxy-2-diglycolylimido-β-D-glucopyranoside 

Downstream Products

• 121123-45-3 3,4,6-tri-O-benzyl-2-acetamido-2-deoxyamino-α-D-glucopyranose 
• 1330629-86-1 C₄₁H₄₈N₂O₈ 
• 1330629-85-0 C₃₇H₄₈N₂O₈ 
• 1330629-92-9 C₅₆H₇₃N₉O₁₅ 
• 1330629-91-8 C₅₀H₆₂N₄O₁₂ 
• 1330629-90-7 C₅₃H₆₁N₃O₁₂ 
• 1330629-89-4 C₅₂H₅₉N₃O₁₁ 
• 1330629-88-3 C₄₈H₅₉N₃O₁₁ 
• 129729-36-8 6-O-acetyl-3,4-di-O-benzyl-2-deoxy-2-p-methoxybenzylideneamino-α,β-D-glucopyranosyl chloride 
• 129729-53-9 methyl 4-O-(6-O-acetyl-3,4-di-O-benzyl-2-deoxy-2-p-methoxybenzylideneamino-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 129729-47-1 methyl 6-O-(6-O-acetyl-3,4-di-O-benzyl-2-deoxy-2-p-methoxybenzylideneamino-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 129729-34-6 2-amino-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranose hydrochloride 
• 129729-35-7 3,4-di-O-benzyl-2-deoxy-2-p-methoxybenzylideneamino-β-D-glucopyranose 
• 4171-71-5 2-benzamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose 

Relevant academic research and scientific papers

Conversion of the N-Benzylacetamido Group into the Acetamido Group by Autoxidation in Potassium t-Butoxide-Dimethyl Sulphoxide

The N-benzylacetamido group is rapidly converted into the acetamido group at 20 deg C by the action of molecular oxygen in a solution of potassium t-butoxide in dimethyl sulphoxide and a general route to acetylated amines by the alkylation of N-benzylacet

Why Is Direct Glycosylation with N-Acetylglucosamine Donors Such a Poor Reaction and What Can Be Done about It?

The monosaccharide N-acetyl-d-glucosamine (GlcNAc) is an abundant building block in naturally occurring oligosaccharides, but its incorporation by chemical glycosylation is challenging since direct reactions are low yielding. This issue, generally agreed upon to be caused by an intermediate 1,2-oxazoline, is often bypassed by introducing extra synthetic steps to avoid the presence of the NHAc functional group during glycosylation. The present paper describes new fundamental mechanistic insights into the inherent challenges of performing direct glycosylation with GlcNAc. These results show that controlling the balance of oxazoline formation and glycosylation is key to achieving acceptable chemical yields. By applying this line of reasoning to direct glycosylation with a traditional thioglycoside donor of GlcNAc, which otherwise affords poor glycosylation yields, one may obtain useful glycosylation results.

Formation of 2-acetamido-2-deoxy-d-glucopyranosidic linkages via glycosidation using a combination of two lewis acids

A mixed activation system composed of ytterbium(III) triflate and a catalytic boron trifluoride diethyl etherate complex efficiently promotes the glycosylation of various alcohol acceptors using 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl ac

Order of reactivity of OH/NH groups of glucosamine hydrochloride and N -Acetyl glucosamine toward benzylation using NaH/BnBr in DMF

The order of reactivity of OH and NH groups of glucosamine hydrochloride (GlcNH2HCl) and N-acetyl glucosamine (GlcNAc) toward benzylation with NaH/BnBr in DMF was investigated. For GlcNH2.HCl, benzyl groups were introduced in the order of N-Bn > N-Bn2 > 1-O-Bn > 6-O-Bn > 4-O-Bn > 3-O-Bn; for GlcNAc, benzyl groups were introduced in the order of 1-O-Bn > 6-O-Bn > 4-O-Bn > 3-O-Bn > N-Bn. A range of partially benzylated 2-N,N′-dibenzyl glucopyranosides and GlcNAc derivatives were obtained in a single step. Taylor & Francis Group, LLC.

Formation of 1,2-CIS-α-aryl-glycosidic linkages directly from 2-acetamido-2-deoxy-D-glucopyranosyl acetate by the mixed activating system using ytterbium(III) triflate and catalytic boron trifluoride diethyl etherate complex

We found that a mixed activating system using ytterbium(III) triflate and a catalytic boron trifluoride diethyl etherate complex efficiently promoted glycosidation of the 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D- glucopyranosyl acetate in dichloromethane at room temperature to afford 2-acetamido-2-deoxy-Dglucopyranosides in good yields along with the formation of a considerable amount of α-isomers. Glycosylations of the aryl alcohols as the acceptors stereoselectively afforded aryl α-glycosides without producing any β-isomers.

Synthesis of mimetic peptides containing glucosamine

A convenient synthesis of 2-amino-3,4,6-tri-O-benzyl-2-deoxy-β-D- glucopyranoside was described from the readily available starting material 2-acetamido-2-deoxy-D-glucose (N-acetyl-D-glucosamine). Herein, the coupling of different lipophilic amino acids w

New diacylamino protecting groups for glucosamine

Glucosamine was 'transformed into N-diphenylmaleoyl (DPM), N-(3,3-dimethylglutaryl) (DMG), and N-diglycolyl (DG) derivatives which furnished O-acetyl-protected O-glycosyl trichloroacetimidates 3, 12, and 20, respectively, as glycosyl donors. Their reactio

C2-amidoglycosylation. Scope and mechanism of nitrogen transfer

A one-pot C2-amidoglycosylation reaction for the synthesis of 2-N-acyl-2-deoxy-β-pyranosides from glycals is described. Glycal donors activated by the reagent combination of thianthrene-5-oxide (11) and Tf2O, followed by treatment with an amide nucleophile and a glycosyl acceptor, lead to the formation of various C2-amidoglycoconjugates. Both the C2-nitrogen transfer and the glycosidic bond formation proceed stereoselectively, allowing for the introduction of both natural and nonnatural amide functionalities at C2 with concomitant anomeric bond formation in a one-pot procedure. Tracking of the reaction by low-temperature NMR spectroscopy employing 15N- and 18O-isotope labels suggests a mechanism involving the formation of the C2-sulfonium glycosyl imidate 39 as well as oxazoline 37 as key intermediates in this novel oxidative glycosylation process.

Benzyl derivatives of N-2,4-dinitrophenyl-D-glucosamine and their use for oligosaccharide synthesis

Four tri-O-benzyl derivatives of 2-deoxy-2-(2,4-dinitroanilino)-D- glucopyranose were synthesized. Glycosylation using 3,4,6-tri-O-benzyl-2- deoxy-2-(2,4-dinitroanilino)-D-glucopyranose as glycosyl donor and a reagent mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine produced β-glycosides with complete selectivity. Starting from benzyl 3,6-di-O-benzyl-2-deoxy-2-(2,4-dinitroanilino)-β-D- glucopyranoside as acceptor, O-α-D-galactopyranosyl-(1 → 4)-O-β-D- galactopyranosyl-(1 → 4)-2-acetamido-2-deoxy-D-glucopyranose, the human blood-group P1-antigenic determinant, was synthesized.